Surprise, Durprise!

1 - Surprising an old friend

It only started out about a year ago. Actually, really, it was much longer ago. But two years ago things REALLY got going. It was when Mike, my brother-in-law, asked me to have a look at his computer, the CDR wasn't doing what it should. So one evening when his wife, my wife's very best friend and business partner, was visiting my wife - it all gets just a bit complicated HERE, anyway, I went over to see what I could do.

After about an hour I thought I had it sorted, it was a software rather than a hardware problem. I shouted down to Mike to show him what I'd done but when I called he wasn't there. Probably gone over the road to see his wife, or mine maybe. I said it was complicated.

Mike and I had been mates for donkey's years, ever since school sixth form. Done everything together, even dated best friends, Marianne and Carol. And yes, even married them. OK, we'd all split up to go to college, the girls both got into Cambridge, I went to Exeter, Mike went to Oxford so we were some distance apart but we still met up in holidays and for weekends and so on. Mike stayed on to do his Master's, I left and got a job and married Carol about 6 months later, we reckoned we could afford it by them, both working and so on. Mike and Mari got hitched another 6 months after that just after he started work.

And we all lived near Brum, we liked the area, felt accepted there, on different sides of the city to start with but later we ended up in two nice houses on opposite sides of the road, and only about 100 yards apart. The girls were delighted, living so near to each other, they ended up setting up their own small business together, and Mike and I still got on really famously.

Anyway, back to THE day. The first day. The very first day that I realised my mate of long-standing had an interest I hadn't known about. When I realised Mike wasn't around I decided to have a bit of a play, to see just what Mike's so-called 'super-computer' was about. It wasn't really super, just quite a bit newer than mine. From the Desktop I clicked on 'Documents' and saw - to my surprise - a filename which surprised me. It surprised me a lot.

'Jennyinlondon.jpg.'

I recognised the name. I'd seen it before. I'd downloaded it. I clicked to be sure and - yes. I was right. Mike had been careless, he shouldn't have left the shortcut there, he should have deleted it but he hadn't. I looked. At an attractive woman on a street probably in London, chatting to a street vendor of some sort. An attractive woman, I have to say, but then like I said I'd seen it before. And other pictures of Jenny in different places and in different poses. Including pictures of her in very smart and attractive dresses, or in exotic skimpy lingerie, or even in school uniforms. And others where, proudly protruding from under her skirt you could see her cock. Jenny was a transvestite, probably still is. I'd never met one, never even seen one in real life except maybe one day in Centenary Square in Brum but I wasn't really sure about that one. If I hadn't had Carol with me at the time I might well have followed her. Him. Or her, followed her to try to find out.

But on the Web, that's different. I'd seen lots. Absolutely loads. I loved to look at the ultra-feminine figures and faces and legs and hair of men dressed as women. But Mike - that surprised me. I'd known him for years, never suspected ...

"Well Ben. You too?"

Mike had surprised my day-dreaming, I hadn't heard him come into the study - the small bedroom really. And what he had said and the tone of his voice had surprised me too. How long had I known Mike? Years, obviously. Yet I had never realised, and neither had he, that we shared a common interest, a common fascination, with TVs. Trannies. Transvestites. Men who liked to dress up in women's clothes. I smiled, rather weakly, at him.

"Well, I think the CDR is fixed, mate. PC up and fully running."

Mike didn't say anything. He just reached up to the CD rack beside the PC and took a disc from it, one hand-labelled 'footy pics'. He leaned over my shoulder to put it into the machine, then took the mouse and clicked through the directories. He double-clicked a file, I didn't see which, and on-screen appeared a picture of a woman. Except I knew, I KNEW, it wasn't a woman. This was a tranny, sitting in a café somewhere smiling as 'she' reached for her coffee cup. You could see people all around the edges of the picture, obviously this was a tranny who was 'out', or at least one who went out dressed up.

And dressed? Well! The image was outstanding. A 'woman' with longish red hair, gorgeous makeup, tasteful but good-looking jewellery, and a wonderfully sexy outfit - white blouse deep cut at the front to show some cleavage, short tight black skirt, stockings and high heeled shoes. I'm sure they were stockings. I looked at the picture. Then I looked at Mike. He smiled at me.

"That's Rebecca, somewhere in the States, Ohio I think, my favourite tranny. She just looks so gorgeous. If she wasn't a man I could fuck her, really. What do you think?"

I had to agree with him, and countered his efforts by going online and finding 'Kathleen' - an English TV he'd not encountered before. Some of her pictures are not that brilliant but when I showed him the series with him/her in a purple latex dress, a gorgeous redhead in black stockings and very high heels his only comment was - Mike always was much cruder than me - "Christ I'd love my cock up that cunt!"

At which point I heard a noise from downstairs - the girls were back. Mike quickly took charge of the mouse and logged off quickly, ending up on a financial services site in case one of them popped a head into the study. As I left a few minutes later Mike returned to the topic of transvestism.

"You ever dressed yourself, Ben? I bet you have. I did a bit when I was younger, in my mother's stuff. Just a bit you understand. Couldn't do it now though."

Indeed he couldn't. Just before college, having been medium height for all his teen years Mike had shot up. And since then he'd broadened out, to about 6 foot 3 and nearly 14 stone. Not a 'womanly' figure at all. And that's not saying anything about his hairiness, in some ways I'd been jealous of his manly very hairy chest.

I had to admit it - he'd been honest with me.

"Yes, same as you Mike I think, in mother's stuff. And after we got married I did think about dressing in Carol's clothes but really she's way too small."

Carol was not exactly petite but heading that way, certainly more than a whole size less than me in girly clothing terms. His last comment surprised me.

"I bet you could in Mari's clothes, Ben. About size 12, some of them are 14 I know. They'd be about your size I reckon."

I looked at him, somewhat amazed.

"I reckon you should give it a go, mate. Could be fun."

I thought about what Mike had said as I walked home. The idea did appeal, though I was still very surprised he'd mentioned it. And over the next few days, it kept coming into my mind again. Mike didn't say anything, I could tell he hadn't forgotten, but he was waiting for me to say something first. And when, on the Friday afternoon when I got home, my wife said she and Marianne wanted to go shopping in Brum the next day, and would it be OK if they went in my car, the thought of 'dressing' popped into my mind again.

The next day, just after they'd driven off I went over the road and round to Mike's back door. I don't know why really, just seemed the 'safer' thing to do in some way.

"OK Mike, we've got about five hours I reckon. What about this dressing up lark then?"

I wasn't really surprised - he'd thought of it too, he was just about to give me a ring and suggest it. We didn't take all the five hours, it took Mike about half an hour to clear up the stuff he was doing and another half to pick out some things he though suitable. So a couple of hours after going round to his house I was parading round the living room wearing one of Marianne's dresses and a pair of her tights, over a bra and panties and tights. The shoes had been difficult, my feet were over a size too big but I'd found a pair with about 1 1/2 inch heels where I could loosen the ankle strap and slide my feet in. I was worried I might stretch them too much, but Mike said his wife rarely wore that particular pair anyway.

"So - how do I look?" I asked him eventually, sitting on the edge of his sofa and 'provocatively' crossing one nylon-clad leg over the other.

"Actually Ben, not too bad. You surprise me, OK you've not had the chance to choose very carefully or to buy special stuff like lingerie or makeup or a wig. But your figure is not bad, I think the shape of the dress helps."

I looked in the big mirror in the hall. In some ways not bad but in others - well - I was a guy in a frock, and a silly-looking guy at that. I decided to change back, well before the ladies were due to return. We had plenty of time to straighten things out and get them exactly where they had come from and still had an hour to spare.

And that could have been that, been there done that, got the T-shirt etc. In fact over the next couple of weeks, though Mike and I chatted a bit about what we'd done and what we thought about it a few times, when we were on our own, neither of us mentioned a repeat session. Until Carol told me she and Mari had another conference lined up, on a Friday again it was, and said they wouldn't be back until after 10. Which gave us loads of time after work to do just that, have another session though this time Mike had come up with a skirt-and-sweater combination he thought I should try.

And we did it again, and again, three or four times over the next couple of months, trying different outfits of Mari's each time, going just a little further on every occasion. Mike bought some stockings and a suspender belt for 'Bethany' to wear, I got some clip-on earrings and the next time a cheap ladies' watch, and so on.

Then, as the run-in to Christmas began, Mari and Carol were busier and busier in their business, most of the time while Mike and I were both at work but just sometimes at a weekend. At the beginning of December Carol mentioned that the 'girls' would be off in Newcastle the next Saturday, and she hoped we wouldn't mind, or maybe we'd like to come along too, make a weekend of it. I umm-ed and aah-ed at the suggestion, by that time I was really getting into the dressing up lark and I'd had a couple of thoughts, a full day at it would be wonderful. As it was Mike had to say no in the end, he had a client who was staying in Brum Friday night, needed 'client-sitting', looking after the evening before.

And I was a bit busy that Friday evening too, I didn't see Mike at all until I went round to see how he was getting on at about 9 on the Saturday morning.

"OK Ben. Time for Bethany, do we think? I've got a surprise for you, went shopping on Wednesday, something I'd like to see you in. How about it?"

If Mike hadn't suggested it I'd have done so myself. I had a couple of surprises for him too. Shoes, I'd managed to find a pair to fit. OK my feet aren't massive but in Ladies' terms they are big. In a factory shop I passed on my way back from work every day, while looking for a pair of ordinary men's shoes for me I had looked over the women's section briefly and come up with 3 pairs which I had thought would fit. They hadn't been particularly expensive and I'd bought the lot as well as the pair of ordinary black shoes I'd gone in for.

I hadn't had time to be embarrassed, in fact the sales assistant hadn't even looked in the boxes, she just scanned their codes and asked me to sign the card receipt. When I got home I'd tried them, with a pair of Carol's tights over my feet to get the right thickness. Perfect. I felt very pleased with myself. I could have tried on the stockings I'd bought too, in the supermarket, but didn't want to go too far, not at home, not with Carol due soon.

"OK Ben, how about this?" asked Mike, holding up one or Mari's dresses.

It was a simple black number, quite similar to one of Carol's which I'd always thought she looked good in. Your actual basic LBD. The dress looked good, but the size didn't. It was bigger than Carol's LBD but I had doubts about getting into it and said so.

"OK then how about - voila!"

Mike held up something. I couldn't see what at first, then I realised. Any self-respecting tranny admirer should have recognised it at once but I just wasn't expecting it, and the light caught the clear plastic packaging rather oddly at first. But I got it as soon as Mike moved it. It was a basque. A black lace-up basque, one of the 'figure enhancers' I'd seen in tranny magazines and on so many TV pictures online. Black, shiny, and tight. I gasped a little.

"I reckon with that on, Ben, you can get into the dress, and what about this as well?"

It was obvious Mike was feeding some fetish of his. Like many men, me included, long willowy blondes feature high up on our list of desirable females. Indeed Mike had married one. Well, long, blonde, and not too far from willowy at least.

"So I'm to be Marianne, am I?" I suggested. "Just because you couldn't get her into a black basque."

"No, Ben. No, definitely not. It's just when I went into the sex shop, you know, the new one in the City centre, near that PC shop you almost live in sometimes, they had this on special offer. Less than half price. And a wig might make such a difference. I think so anyway. So, how about it? Want to give it a go?"

At which point Mike's mobile beeped, he'd changed the ringtone. I'd told him 'The Sting' was a naff tune and he'd put on something else which that first time I didn't recognise. I did later!

He answered it, muttered a bit, mainly listening, then said "OK, about twenty minutes?" and rang off.

"The Rugby Club. The treasurer's not there so I have to go down, I'm the only one they can find with the keys to the safe. Well, want to do it while I'm gone? No wives until late tonight. OK?"

I thought. Didn't take me long, the thought of the basque, and the wig, and the shoes I'd brought, together they sent a bit of a tingle down my spine. And elsewhere.

"OK then Mike. I'll give it a go."

2 - Dressed to surprise

He really did have to dash off, I knew he'd get to the club in about a quarter of an hour the way he drove, it would have taken me about twice the time. But he had the sort of car you just have to drive fast - to justify buying it really. I set to, looking out the black panties I'd brought, they would go well with the basque, well, the bustier really, it was a combined job, bra and 'cincher', that's the name, just couldn't think of it for a moment. Not a word you come across in everyday language.

I stripped and showered first, pulling the panties on tight. Then the basque, that was a bit of a nightmare. It really was rather tight, very elasticated but I could feel it doing its job. And when I pulled on the lacings, well. It was some piece of engineering, let me tell you. As I pulled tighter and looked in the mirror I could see my waist shrinking, but also the small amount of 'spare flesh' I had round my waist, that seemed to be pushed upwards and to mould itself into the cups of the bra section. That, together with the slight padding under the bra cups, combined to give me something approaching the 'hourglass' figure beloved of all trannies worldwide. I realised now how some of the guys - the trannies that is - I'd seen on the web did it. With that basque or an even better quality version, a femme figure really was achievable.

Quite what Mike expected to find when he came back I didn't know but I wanted to do as good a job as I could, not for him, for me. I was heading down the road to full-blooded tranny-ism, and I liked it!

The stockings came next. Yes, stockings. Black and quite sheer, not seamed though, I'd thought that would be going too far. I slid them up my thighs, enjoying that classic TV feeling, and clipped them to the straps at the bottom of the basque-cum-bustier. It felt good. Very good. I slid my toes into the black high heels I'd bought, the ones with about a 4 inch heel, and stood up. For the first time in shoes properly my size, and for the first time in such high heels. I walked steadily round the room, loving the feeling of my nylon-clad thighs rubbing together as I walked, and enjoying the high-heel experience for the first time really. It was fun, it felt so good, and I was thrilled I coped so well with the heels. When I looked in the mirror again - really I was a little disappointed. A man in a frock, well, no, in a basque actually, but a man definitely, and a rather silly-looking one at that.

But I had to get on. I hadn't finished yet. My other slight surprise for Mike and for myself was a gift-pack of make-up items, good quality, I'd splashed out on at the Selfridges in the town centre. I'd read comments online from trannies, one thing several had said was that you should always use good quality make-up, that cheap stuff may seem as good but it wasn't. So I'd looked for a gift pack, one with all the bits in, and found one by Dior, yet again at a reduced price, just like the wig Mike had bought.

And in the previous week, on two occasions when Carol had been out in the evenings, I'd had time to practice a bit, to look at some of the hints and tips in a couple of her magazines. I laid out the items, the blusher, the eye-shadow, the eye-liner and so on beside Mari's own stuff on her dressing table in the bedroom, looking carefully where I put things and at her stuff so I would be able to leave everything just as I'd found it. I set to, carefully and methodically, a little foundation first, then covering the whole face but not too thickly. Blusher, mascara, eye-shadow, eyeliner, eyebrow pencil, all meticulously applied as I'd practiced and as I'd seen in the magazines.

I loved the experience, the artistic efforts needed, as I progressed I began to feel more and more feminine, to actually feel like a woman 'putting on her face' before going out or something. The lipstick came last, very steadily and slowly outlining my own lips with what I thought was a cute 'cupid's bow' in the middle of the top lip. I used a thin lip-liner to finish, then a slight covering of lip-gloss.

Finally, the wig. It wasn't quite as long as I'd first thought, nor yet quite as blonde, I didn't know quite how wigs were sized and I don't think Mike did either, But it did fit smoothly and snugly over my head, covering up absolutely all of my own thinning and slightly darker hair. I clipped the two tiny clips into place behind the ears and gave the whole wig a bit of a brushing, feeling it pull down on the clips, it felt tight. But secure. Then I looked at the whole facial effect.

And this time - I felt good. Very good, The man in a frock, or whatever, had gone. Nowhere to be seen. And in 'his' place was a woman. An attractively made-up blonde woman, maybe a little younger than me but - I did think I might have been misleading myself at the time but I genuinely did believe it - female. Most definitely female. I loved it!

And I'd nearly finished. The stick-on nails, a bright-ish red to match my lips I hoped, were in fact easier to put on than I'd feared. The fake gold hoop earrings looked good too, clipped to the lobes of my ears, showing clearly under my longish blonde locks. I had a quick look in Mari's little jewellery box and found what I wanted, something I'd seen her wearing before, a black velvet 'choker' with a single gold oval-shaped embellishment at its centre. I tied it on and then slid onto my fingers about five of the cheap costume ring's I'd bought, basically fitting them onto whichever fingers they fitted. The ladies' watch came last, then I stood and turned to reach for Marianne's little black dress.